Tetrahydrofuran → 4-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

HRID 991489ノート

反応式

HRID 991489 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:26]=[CH:25][C:11]([O:12][CH:13]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:14][CH:15]=[CH2:16])=[CH:10][CH:9]=1.C1C[O:30]CC1>CCOCC>[OH:30][CH2:16][CH2:15][CH2:14][CH:13]([C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[O:12][C:11]1[CH:25]=[CH:26][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 8028TetrahydrofuranHCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

生成物 1

HCID 222354084-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-5 °C

実験手順

4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (from step (i) above; 4.6 g; 13 mmol) was dissolved in dry THF (50 mL) under argon and cooled to −5° C. Borane-methylsulfide complex (BH3xSMe2) (3.5 mL of a 2 M solution in ether) was added dropwise at 0 to 5° C. The mixture was stirred at that temperature for 1.5 h. After 4 h at rt, tlc showed that the reaction was complete. The reaction mixture was quenched with 14 mL of H2O and 5 g of NaBO3. The mixture was stirred overnight, the solvent decanted off, and the residue treated with ether and decanted. The combined organic fractions were washed with brine, dried (Na2SO4), and evaporated. The crude product was purified by chromatography on silica (iso-propanol:ethyl acetate:heptane; 5:20:70). Yield: 2.44 g (58%).

後処理

  1. waitAfter 4 h at rt
  2. customThe reaction mixture was quenched with 14 mL of H2O and 5 g of NaBO3
  3. stirringThe mixture was stirred overnight
  4. customthe solvent decanted off
  5. additionthe residue treated with ether
  6. customdecanted
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe crude product was purified by chromatography on silica (iso-propanol:ethyl acetate:heptane; 5:20:70)

出典と根拠

ORDレコード
ord-ae9179b0175c45618723d8240839ed1c
出典データセット
uspto-grants-2002_10
特許番号
US06465481B1

反応ノート

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